EP0447967B1 - Gélification de polymères contenant un acrylamide par l'alcool furfurylique et des aldéhydes hydrodispersibles - Google Patents

Gélification de polymères contenant un acrylamide par l'alcool furfurylique et des aldéhydes hydrodispersibles Download PDF

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Publication number
EP0447967B1
EP0447967B1 EP91103945A EP91103945A EP0447967B1 EP 0447967 B1 EP0447967 B1 EP 0447967B1 EP 91103945 A EP91103945 A EP 91103945A EP 91103945 A EP91103945 A EP 91103945A EP 0447967 B1 EP0447967 B1 EP 0447967B1
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Prior art keywords
acid
sodium
water
acrylamide
ammonium
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EP0447967A3 (en
EP0447967A2 (fr
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Ahmad Moradi-Araghi
Glenn Allan Stahl
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Phillips Petroleum Co
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Phillips Petroleum Co
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/84—Compositions based on water or polar solvents
    • C09K8/86—Compositions based on water or polar solvents containing organic compounds
    • C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
    • C09K8/887—Compositions based on water or polar solvents containing organic compounds macromolecular compounds containing cross-linking agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/04—Aqueous well-drilling compositions
    • C09K8/06—Clay-free compositions
    • C09K8/12—Clay-free compositions containing synthetic organic macromolecular compounds or their precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/50—Compositions for plastering borehole walls, i.e. compositions for temporary consolidation of borehole walls
    • C09K8/504—Compositions based on water or polar solvents
    • C09K8/506—Compositions based on water or polar solvents containing organic compounds
    • C09K8/508—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
    • C09K8/512—Compositions based on water or polar solvents containing organic compounds macromolecular compounds containing cross-linking agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/903—Crosslinked resin or polymer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/935—Enhanced oil recovery

Definitions

  • the present invention relates to a novel process for crosslinking water-soluble polymers utilizing an organic crosslinking system composed of a furan derivative and a water dispersible aldehyde.
  • gelled or crosslinked water-soluble polymers are useful in enhanced oil recovery operations. They have been used to alter the permeability of underground formations in order to enhance the effectiveness of water flooding operations. Polymers along with an appropriate crosslinking system are injected in an aqueous solution into the formation. The polymers then permeate into and gel in the regions having the highest water permeability. Any fluids injected into the formation in subsequent water flooding operations, will then be diverted away from the regions in which the gel formed to areas of the formation now having a higher water permeability.
  • EP-A-0 180 406 discloses a method of treating a subterranean formation for reducing its permeability by contacting it with an aqueous polymerizable composition comprising a polymerization monomer, a polymerization catalyst having a latent period, and an alcoholic compound which is a cyclic ether containing a hydroxymethylene substituent on a carbon atom bonded to the ether oxygen, or an aliphatic alcohol having a carbon-to-carbon double bond or a carbon-to-carbon triple bond.
  • the organic crosslinking system of the present invention is formed from:
  • Furan derivatives suitable for use in the present invention are of the formula: wherein R9, R10, R11, and R12, are independently selected from hydrogen, methyl, hydroxyl, carbinol, carboxyl, -CH2COOH, acyl amide, mercaptan and primary amine radicals, and at least one R9, R10, R11 and R12 radical must be selected from hydroxyl, carbinol, carboxyl, -CH2COOH, acyl amide, mercaptan and primary amine radicals.
  • Suitable furan derivatives include but are not limited to those selected from furfuryl acetate, furanamine, furandiamine, furantriamine, furantetramine, furancarbinol, furandicarbinol (furandimethanol), furantricarbinol, furantetracarbinol, hydroxyfuran, dihydroxyfuran, trihydroxyfuran, tetrahydroxyfuran, furancarboxylic acid, furandicarboxylic acid, furantricarboxylic acid, furantetracarboxylic acid, furanmethylenecarboxylic acid, furanbis(methylenecarboxylic acid), furantris(methylenecarboxylic acid) and furantetrakis(methylenecarboxylic acid), mercaptofuran, and combinations of two or more thereof.
  • the preferred furan derivative for the practice of the present invention is 2-furancarbinol, furfuryl alcohol mercaptofuran, furandicarbinol, furfuryl acetate and furan
  • suitable aldehyde or aldehyde generating compounds can be selected from aliphatic aldehydes, aliphatic dialdehydes, and aromatic aldehydes, aromatic dialdehydes.
  • Preferred aldehydes or aldehyde generating compounds can be selected from formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, heptaldehyde, decanal, glyoxal, glutaraldehyde, terephthaldehyde, hexamethylenetetramine and mixtures thereof.
  • the amount of furan derivative used in preparing the gelled compositions of the invention will be in the range of 0.005 to 5.0 wt.%, preferably from in the range of 0.01 to 2.0 wt.% and most preferably from in the range of 0.05 to 1.0 wt% based on the total weight of the gelable composition.
  • the amount of aldehyde or aldehyde generating compound used will be in the range of 0.005 to 5.0 wt.%, preferably in the range of 0.01 to 2.0 wt.% and most preferably in the range of 0.05 to 1.0 wt% based on the total weight of the gelable composition.
  • the molar ratio of furan derivative to aldehyde or aldehyde generating compound will be in the broad range of 30:1 to 1:30 with a more preferred range of 2:1 to 1:4.
  • water-soluble polymer As used in this application, the term water-soluble polymer, copolymers, and terpolymers refers to those polymers which are truly water-soluble or those which are dispersible in water or other aqueous medium to form a stable colloidal suspension which can be pumped into a formation and gelled therein.
  • the water-soluble polymers which are suitable for use in the present invention include those which contain from 5 to 100 mole percent of at least one monomer of the formula: wherein R1, R2, and R3 are independently selected from hydrogen and alkyl radicals containing from 1 to 3 carbon atoms, of which acrylamide and methacrylamide are the preferred examples; and from 0 to 95 mole percent of at least one monomer selected from
  • the presently preferred class of water-soluble polymers are those selected from homopolymers of acrylamide, homopolymers of methacrylamide, copolymers of acrylamide and acrylic acid, copolymers of acrylamide and sodium acrylate, copolymers of acylamide and N-vinyl-2-pyrrolidone, copolymers of acrylamide and sodium 2-acrylamido-2-methylpropane sulfonate, copolymers of acrylamide and 2-acrylamido-2-ethylpropane sulfonic acid, terpolymers of acrylamide, N-vinyl-2-pyrrolidone, and sodium 2-acrylamido-2-methylpropane sulfonate and terpolymers of acrylamide, N-vinyl-2-pyrrolidone and 2-acrylamido-2-methylpropane sulfonic acid.
  • the ratio of the monomers in the above-described polymers is not critical; provided however, that at least 5 mole percent of acrylamide is present in the above-described polymers.
  • Particularly preferred are terpolymers of N-vinyl-2-pyrrolidone, acrylamide and sodium 2-acrylamido-2-methylpropane sulfonate wherein said monomers are provided in a 30 to 15 to 55 weight percent terpolymer. Additionally within the scope of this invention is the use of combinations of copolymers and terpolymers utilizing the above listed monomers.
  • gelled polymers to alter the water permeability of underground formations is well known to those skilled in the art.
  • an aqueous solution containing the polymer and a crosslinking agent is transmitted into the formation from a well in fluid communication with the formation so that the aqueous solution can diffuse into the more water permeable portions of the formation and alter that water permeability by gelling therein.
  • the present invention can be used in a similar manner.
  • An aqueous solution containing the water-soluble polymer, aldehyde or aldehyde generating compound, and furan derivative is pumped into the formation so that it alters the water permeability of the formation in a similar manner when gelation takes place.
  • the aqueous solution containing the water soluble polymer, aldehyde or aldehyde generating compound and furan derivative can be pumped into the formation in one slug, or alternatively the components may be sequentially injected in a manner to provide an appropriate concentration in the formation.
  • the present invention's advantage lies in the fact that the onset of gelation is delayed allowing the aqueous solution to penetrate further into the formation.
  • the nature of the underground formation treated is not critical to the practice of the present invention.
  • the organic crosslinkers will gel the water-soluble polymers in fresh water, salt water, or brines, as well as at a temperature range of from 93 to 205°C (200 to 400°F).
  • the purpose of this example is to demonstrate the delayed gelation of a water-soluble polymer by a furan derivate and an aldehyde. Additionally this example demonstrates the long term stability of a gel formed with a water-soluble polymer, a furan derivative and an aldehyde.
  • a one percent solution of a terpolymer composed of 30 wt % of N-vinyl-2-pyrrolidone, 15 wt % of acrylamide, and 55 wt % of sodium 2-acrylamido-2-methylpropane sulfonate was prepared in the following manner. 16.3 ml of an inverse emulsion which contained 32.4 wt % of the above-described active terpolymer was mixed with 500 ml of synthetic sea water.
  • the synthetic water used had the following formula:
  • 0.18 ml of furfuryl alcohol was added to 200 ml of the polymer and synthetic sea water mixture described above, to provide a 1000 ppm furfuryl alcohol concentration.
  • 0.36 ml of furfuryl alcohol was added to 200 ml of the polymer and synthetic sea water mixture to generate a 2000 ppm furfuryl alcohol concentration.
  • the ten ampules were sealed under nitrogen and then placed upright in compartmented aluminum boxes with relief holes and placed in an oven and heated to 121°C (250°F). Periodically, the ampules were removed from the oven and the mechanical strength of the gel was determined behind a protective shield.
  • the purpose of this example is to demonstrate the delayed gelation of a water-soluble polymer by a furan derivative and an aldehyde. Additionally this example demonstrates the long term stability of a gel formed with a water-soluble polymer, a furan derivative and an aldehyde at high temperatures.
  • ampules were prepared in a manner identical to those in Example I except that the aging was conducted at 149°C (300°F).

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Formation And Processing Of Food Products (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (8)

  1. Un procédé pour modifier la perméabilité d'une formation souterraine poreuse ayant une température ambiante supérieure à 93°C, caractérisé en ce qu'il consiste à introduire dans ladite formation soit indépendamment, soit en mélange :
    (a) 0,1 à 5 % d'un polymère soluble dans l'eau constitué de
    (a1) 100 à 5 moles % d'au moins un monomère de formule (I)
    Figure imgb0037
        dans laquelle R₁, R₂ et R₃ sont choisis indépendamment parmi l'hydrogène et les radicaux alkyle renfermant de 1 à 3 atomes de carbone et
    (a2) 0 à 95 moles % d'au moins un monomère choisi parmi
    (i) monomère de formule II
    Figure imgb0038
        dans laquelle R₄ est choisi parmi l'hydrogène et les radicaux alkyle renfermant de 1 à 6 atomes de carbone, R₅ est choisi parmi les radicaux alkylène renfermant de 1 à 6 atomes de carbone et les radicaux arylène renfermant de 6 à 10 atomes de carbone et M est choisi parmi l'hydrogène, l'ammonium, le potassium et le sodium.
    (ii) un monomère de formule III
    Figure imgb0039
        dans laquelle R₆, R₇ et R₈ sont choisis indépendamment parmi l'hydrogène et les radicaux alkyle renfermant de 1 à 2 atomes de carbone; et
    (iii) un monomère choisi parmi l'acide acrylique, l'acrylate de sodium, l'acrylate de potassium, l'acrylate d'ammonium, l'acide méthacrylique, le méthacrylate de sodium, le méthacrylate de potassium, le méthacrylate d'ammonium, l'acide vinylsulfonique, le vinylsulfonate de sodium, le vinylsulfonate de potassium, le vinylsulfonate d'ammonium, l'acide vinylbenzyl-sulfonique, le vinylbenzyl-sulfonate de sodium, le vinylbenzylsulfonate de potassium, le vinylbenzyl-sulfonate d'ammonium, l'acétate de vinyle, l'acrylonitrile, le métha-cryloni-trile, un vinyl-alkyl-éther, le chlorure de vinyle, l'anhydride maléique, les composés d'ammonium quaternaire cationiques substitués par un radical vinyle, le méthyl-sulfate de (acryloyloxyéthyl)diéthylméthylammonium et les mélanges de deux ou plusieurs de ceux-ci;
    (b) 0,005 à 5,0 % d'un aldéhyde ou d'un composé générant de l'aldéhyde pouvant être dispersé dans l'eau
    (c) 0,005 à 5,0 % d'un dérivé de furane de formule IV
    Figure imgb0040
    dans laquelle R₉, R₁₀, R₁₁ et R₁₂ sont choisis indépendamment parmi l'hydrogène, un radical méthyle, hydroxyle, carbinol, carboxyle, -CH₂COOH, acyl amide, mercaptan et amine primaire et au moins l'un de R₉, R₁₀, R₁₁ et R₁₂ est choisi parmi un radical hydroxyle, carbinol, carboxyle, -CH₂CCOH, acylamide, mercaptan et amine primaire ; et
    (d) 85 à 99,89 % d'eau
       où tous les pourcentages sont des pourcentages en poids calculés sur le total de tous les constituants (a) à (d) et permettant aux constituants (a) à (d) de former un gel dans ladite formation souterraine poreuse.
  2. Le procédé selon la revendication 1 dans lequel ledit polymère (a) soluble dans l'eau est choisi parmi les homopolymères d'acrylamide, les homopolymères de méthacrylamide, les copolymères d 'acrylamide et d'acide acrylique, les copolymères d'acrylamide et d'acrylate de sodium, les copolymères d'acrylamide et de N-vinyl-2-pyrrolidone, les copolymères d'acrylamide et de 2-acrylamido-2-méthylpropane sulfonate de sodium, les copolymères d'acrylamide et d'acide 2-acrylamido-2-méthylpropane sulfonique, les terpolymères de N-vinyl-2-pyrrolidone, d'acrylamide et de 2-acrylamido-2-méthylpropane sulfonate de sodium et les terpolymères d'acrylamide, de N-vinyl-2-pyrrolidone et d'acide 2-acrylamido-2-méthylpropane sulfonique.
  3. Procédé selon les revendications 1 ou 2 dans lequel le dérivé de furane (c) est choisi parmi l'acétate de furfuryle, la furanamine, la furandiamine, la furantriamine, la furantétramine, le furancarbinol, le furandicarbinol, le furantricarbinol, le furantétracarbinol, l'hydroxyfurane, le dihydroxyfurane, le trihydroxyfurane, le tétrahydroxyfurane, l'acide furancarboxylique, l'acide furandicarboxylique, l'acide furantricarboxylique, l'acide furantétracarboxylique, l'acide furanméthylènecarboxylique, le furanbis(acide méthylène carboxylique), le furantris(acide méthylène carboxylique), le furantétrakis(acide méthylène carboxylique), le mercaptofurane et des combinaisons de deux ou plusieurs de ceux-ci.
  4. Le procédé selon l'une quelconque des revendications précédentes dans lequel ledit aldéhyde ou ledit composé générant de l'aldéhyde (b) est choisi parmi le formaldéhyde, le paraformaldéhyde, l'acétaldéhyde, le propionaldéhyde, le butyraldéhyde, l'isobutyraldéhyde, le valéraldéhyde, l'heptaldéhyde, le décanal, le glyoxal, le glutaraldéhyde, le téréphtaldéhyde, l'hexaméthylènetétramine et leurs mélanges.
  5. Le procédé selon l'une quelconque des revendications précédentes dans lequel les constituants (a) à (d) sont utilisés dans les quantités suivantes:
    Figure imgb0041
  6. Le procédé selon l'une quelconque des revendications précédentes dans lequel ledit polymère (a) soluble dans l'eau est un terpolymère de N-vinyl-2-pyrrolidone, d'acrylamide et de 2-acrylamido-2-méthylpropane sulfonate de sodium, ledit dérivé de furane (b) est l'alcool furfurylique et ledit aldéhyde ou composé générant de l'aldéhyde (c) est le formaldéhyde.
  7. Une composition de gel susceptible d'être obtenue par gélification des constituants suivants:
    (a) 0,1 à 5 % d'un polymère soluble dans l'eau constitué de :
    (a1) 100 à 5 moles % d'au moins un monomère de formule I
    Figure imgb0042
        dans laquelle R₁, R₂ et R₃ sont choisis indépendamment parmi l'hydrogène et les radicaux alkyle renfermant de 1 à 3 atomes de carbone, et
    (a2) 0 à 95 moles % d'au moins un monomère choisi parmi :
    (i) un monomère de formule II
    Figure imgb0043
        dans laquelle R₄ est choisi parmi l'hydrogène et les radicaux alkyle renfermant de 1 à 6 atomes de carbone, R₅ est choisi parmi les radiaux alkylène renfermant de 1 à 6 atomes de carbone et les radicaux arylène renfermant de 6 à 10 atomes de carbone et est choisi parmi l'hydrogène, l'ammonium, le potassium et le sodium ;
    (ii) un monomère de formule III
    Figure imgb0044
        dans laquelle R₆, R₇ et R₈ sont choisis indépendamment parmi l'hydrogène et les radicaux alkyle renfermant de 1 à 2 atomes de carbone et
    (iii) un monomère choisi parmi l'acide acrylique, l'acrylate de sodium, l'acrylate de potassium, l'acrylate d'ammonium, l'acide méthacrylique, le méthacrylate de sodium, le méthacrylate de potassium, le méthacrylate d'ammonium, l'acide vinylsulfonique, le vinylsulfonate de sodium, le vinylsulfonate de potassium, le vinylsulfonate d'ammonium, l'acide vinylbenzylsulfonique, le vinylbenzylsulfonate de sodium, le vinylbenzylsulfonate de potassium, le vinylbenzylsulfonate d'ammonium, l'acétate de vinyle, l'acrylonitrile, le méthacrylonitrile, un vinyl-alkyl-éther, le chlorure de vinyle, l'anhydride maléique, les composés d'ammmonium quaternaire cationiques substitués par un radical vinyle, le méthylsulfate de (acryloyloxyéthyl)diéthyl-méthylammonium, et les mélanges de deux ou plusieurs de ceux-ci.
    (b) 0,005 à 5,0 % d'un aldéhyde ou d'un composé générant de l'aldéhyde pouvant être dispersé dans l'eau
    (c) 0,005 à 5,0 % d'un dérivé de furane de formule IV
    Figure imgb0045
       dans laquelle R₉, R₁₀, R₁₁ et R₁₂ sont choisis indépendamment parmi l'hydrogène, un radical méthyle, hydroxyle, carbinol, carboxyle, -CH₂COCH, acyl-amide, mercaptan et amine primaire et au moins l'un de R₉, R₁₀, R₁₁ et R₁₂ est choisi parmi un radical hydroxyle, carbinol, carboxyle, -CH₂COOH, acrylamide, mercaptan et amine primaire, et
    (d) 85 à 99,89 % d'eau
       où tous les pourcentages sont des pourcentages en poids calculés sur le total de tous les constituants (a) à (d).
  8. La composition de gel selon la revendication 7 dans laquelle un ou plusieurs des constituants (a), (b), (c) et (d) sont comme définis dans l'une quelconque des revendications 2 à 6.
EP91103945A 1990-03-15 1991-03-14 Gélification de polymères contenant un acrylamide par l'alcool furfurylique et des aldéhydes hydrodispersibles Expired - Lifetime EP0447967B1 (fr)

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US07/493,665 US5043364A (en) 1990-03-15 1990-03-15 Gelation of acrylamide-containing polymers with furfuryl alcohol and water dispersible aldehydes
US493665 1990-03-15

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EP0447967A2 EP0447967A2 (fr) 1991-09-25
EP0447967A3 EP0447967A3 (en) 1991-11-27
EP0447967B1 true EP0447967B1 (fr) 1994-05-18

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EP (1) EP0447967B1 (fr)
AU (1) AU625168B2 (fr)
CA (1) CA2035423C (fr)
EG (1) EG19032A (fr)
ES (1) ES2053225T3 (fr)
MX (1) MX171813B (fr)
NO (1) NO301079B1 (fr)
NZ (1) NZ237342A (fr)

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US4939203A (en) * 1983-07-18 1990-07-03 Cities Service Oil And Gas Corporation Gel for retarding water flow
US4600057A (en) * 1984-10-23 1986-07-15 Halliburton Company Method of reducing the permeability of a subterranean formation

Also Published As

Publication number Publication date
NO301079B1 (no) 1997-09-08
CA2035423C (fr) 1994-10-18
EP0447967A3 (en) 1991-11-27
NZ237342A (en) 1992-06-25
ES2053225T3 (es) 1994-07-16
NO911026L (no) 1991-09-16
EP0447967A2 (fr) 1991-09-25
AU7264191A (en) 1991-09-19
EG19032A (en) 1994-04-30
CA2035423A1 (fr) 1991-09-16
NO911026D0 (no) 1991-03-14
AU625168B2 (en) 1992-07-02
MX171813B (es) 1993-11-16
US5043364A (en) 1991-08-27

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